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The 11 Best Things to Do in Woodstock, Vermont

Woodstock, Vermont, is considered one of the most beautiful small towns in the United States. In fact, this charming place draws visitors from all over the world to make their way through New England. Especially in the fall, Woodstock is full of leaf peepers from nearby states, such as Massachusetts, New York, New Jersey, Connecticut, and New Hampshire. Therefore, we suggest visiting during the week, if possible, to avoid the high season crowds. Woodstock is also an extremely pet-friendly destination, so bring the whole family–including Fido–on your vacation!

In this article, we’ll review the 11 best things to do in Woodstock, Vermont, including top activities, nearby hiking trails, and places to take pictures. Plus, we’ll reveal the best places to eat and where to stay in Woodstock so you can plan the best vacation possible. Please note that we’ve also included a few things to do in Quechee in this list since it’s so close by!

Disclaimer: This article contains affiliate links. I may earn a small commission when you book an activity or reservation through these links at no extra cost to you.

The best things to do in Woodstock (& Quechee!)

Historic homes in Woodstock, VT along Pleasant Street decorated for fall.

Historic homes along Pleasant Street in Woodstock, Vermont.

Visit Marsh-Billings-Rockefeller National Historical Park.

You can find some of the best outdoor activities in Woodstock at Marsh-Billings-Rockefeller National Historical Park, featuring over 20 miles of trails and carriage roads. The property’s name refers to its many famous owners: George Perkins Marsh, Mary Montagu Billings French, Laurance Rockefeller, and Mary French Rockefeller. Interestingly, this historical park is the only national park in the state of Vermont!

Some of the most popular hikes here include the Faulkner Trail and the Hike to the Pogue. However, if you’d like to spend even more time here, we recommend extending either of these treks to include Mount Tom. The panoramic view of Woodstock from the summit is not to be missed! For a complete list of hiking trails at Marsh-Billings-Rockefeller National Historical Park, click here

The Marsh-Billings-Rockefeller Mansion does not currently offer full tours of the home. However, even if you can’t take a guided tour, you can still enjoy the mansion’s gardens! Parking is shared with the Billings Farm & Museum, and we suggest dropping by the Visitor Center if you have any questions.

Pro tip: Due to the climate, the hikes at Marsh-Billings-Rockefeller National Historical Park are best enjoyed from April to October.

Experience a fully operating dairy farm at Billings Farm & Museum.

View of Billings Farm & Museum in the fall.

View of Billings Farm & Museum in Woodstock, VT the fall.

Just down the road from Woodstock Village, you’ll come across Billings Farm & Museum. This outdoor history museum serves as an operating dairy farm and a gateway to Vermont’s rural past. Especially if you’re traveling to Vermont with kids, Billings Farm & Museum is a must-do activity in Woodstock. Plan to spend at least two hours here to experience the interactive programs, including events like milking and cheesemaking demonstrations. Another big plus is that petting the animals is encouraged!

Don’t miss the Dairy Bar, located on the bottom floor of the 1890 Farm Manager’s House. Here, you can sample Vermont-made ice cream, Billings Farm cheddar cheeses, and maybe even a fresh cider donut (available in the fall)! For more information about the cost of admission and operating hours for Billings Farm & Museum, click here. You can also check to see if there are any special activities planned for the day of your visit here.

Explore downtown Woodstock on foot.

Historic Ebenezer Fitch House in Woodstock, Vermont in the fall.

The Historic Ebenezer Fitch House on The Green in Woodstock, VT.

One of the best activities in Woodstock is to take your time to walk around and fully experience the town. We suggest parking near the central square, called the Green. Then, make your way down the main road, Central Street, and later cross onto Elm Street, towards the Ottauquechee River. Strolling through Woodstock Village truly feels like taking a step back in time! On your walk, check out some of the town’s highlights: the 1883 Norman Williams Public Library and the historic hotel Woodstock Inn.

An extraordinary time of year to visit Woodstock is during October, when you’ll see the homes surrounded by fall foliage, pumpkins, and Halloween decorations! Furthermore, Christmas is a popular season to experience the town covered in festive lights, wreaths, and other adornments.

Shop ’til you drop in Woodstock Village.

Don’t forget to pick up some souvenirs on your trip to Woodstock! One of the top things to do in town is undoubtedly to shop at the many boutiques and mom-and-pop stores. To help plan your shopping excursion, here are five local businesses to visit while you’re in Woodstock:

  • The Yankee Bookshop opened in 1935, making it the longest-running independent bookstore in the state of Vermont. Here, you’ll find a wide selection of books, gifts, cards, vinyl records, and stationery in a cozy environment.
  • Clover Gift Shop features carefully curated gifts, home decor, and CBD products. This shop was founded in 1928 and has since become the go-to place to find unique Vermont souvenirs. For example, discover handmade mugs and jewelry, locally-produced maple syrup, and other Vermont-made gifts.
  • F.H. Gillingham & Son’s has been a Woodstock institution since 1886. Nowadays, this general store is best-known for its high-quality Vermont products, such as maple syrup, cheeses, sweets, clothing, and gifts.
  • The Vermont Flannel Company sells an important Vermonter staple: soft and warm flannel made in the USA! You can find everything from flannel shirts and pajamas to flannel blankets in this store.
  • Danforth Pewter opened in Woodstock over 40 years ago and sells handcrafted pewter gifts made in Vermont. Some of their most coveted products include one-of-a-kind oil lamps, ornaments, jewelry, vases, and picture frames.

Admire the covered bridges around town.

Middle Covered Bridge in downtown Woodstock, VT.

Middle Covered Bridge in the fall in downtown Woodstock.

Did you know that the state of Vermont is famous for its high concentration of covered bridges? Conveniently, these structures are both historic and a great opportunity for photos! While in Woodstock, there are four main covered bridges nearby: Middle Covered Bridge, Taftsville Covered Bridge, Lincoln Covered Bridge, and Quechee Covered Bridge (near Simon Pearce Mill).

If you only have time to visit one, we recommend walking by Middle Covered Bridge as you explore Woodstock Village. This 139-foot-long bridge was built in 1969 to replace an old iron bridge and sits next to The Green. Furthermore, it’s one of the most popular Instagram spots in Woodstock!

Read More: The 14 Best Things to Do in Stowe, Vermont

Sample Vermont maple syrup and cheese at Sugarbush Farm.

Sugarbush Farm sits just five miles outside of Woodstock and is the perfect place to visit with the whole family. Kids love seeing the farm animals, the drive up to the farm is absolutely stunning, and admission is free! Plus, you can pick up some local souvenirs here, such as Vermont maple syrup made on the farm and cheeses, too. In fact, this family-owned farm produces 15 kinds of waxed cheese and 4 grades of pure maple syrup.

As you explore the property, you’ll learn all about the syrup-making process, beginning with tree tapping. Although the actual maple syrup-making season is in the spring (March and April), luckily, the farm offers a year-round display. Moreover, you’ll get to sample syrup and cheese on your visit before passing through the gift shop.

Before you head out, don’t miss the short nature trail behind the parking lot! Here, you can take a walk among the maple trees and see the chapel built by Jeff Luce. Remember that Sugarbush is a fully operational farm, so its hours are from 9-5 every day.

Hike the Quechee Gorge Trail.

View of Quechee Gorge from Route 4 Bridge

View of Quechee Gorge from the Route 4 bridge in Quechee, VT.

If you’re looking for hiking near Woodstock, we highly recommend checking out the Quechee Gorge Trail. This 2.7-mile easy trek is within Quechee State Park and features some beautiful views of the Ottauquechee River and Quechee Gorge. In case you didn’t know, many people refer to this gorge as “Vermont’s Little Grand Canyon”! If you’d like to make the hike a little shorter, you can park at the visitor center and begin the walk to the bottom of Quechee Gorge from there.

There’s normally plenty of parking at this location, making it an easy outdoor activity to do on your visit to Woodstock. Additionally, for more information, you can find an official trail guide here. Remember to always check the weather before beginning to hike and to prepare accordingly. Due to the climate, this trail is most frequented between April and October.

Pro tip: Make sure to walk over the Route 4 bridge. This spot is one of the best places to take pictures of Quechee Gorge!

Shop local at Woodstock Farmers’ Market.

The Woodstock Farmers’ Market is open year-round, serving the community with delicious local food in two locations: Woodstock and Waterbury, Vermont. However, in this particular scenario, we are of course recommending you drop by the Woodstock storefront! This gourmet grocery store offers all sorts of gourmet products, including fresh organic produce, grab-and-go sandwiches, coffee and espresso, baked goods, meats and cheeses, and other Vermont-made food items. Plus, the Woodstock location sits a convenient three-minute drive from the historic village.

On your visit, we suggest picking up sandwiches as a quick and easy lunch–the Moonlight in Vermont is a customer favorite! If you’d like to see all the options for to-go food, you can read the full grab-n-go menu here. Additionally, the Farmers’ Market makes a great stop on a Vermont road trip to rest and recharge with a coffee and freshly baked pastries. Before you stop by, remember that the market is closed on Mondays! Its current hours are from 9 a.m.-5 pm. Tuesdays through Sundays.

Take a photo at the instagrammable Sleepy Hollow Farm.

View of Sleepy Hollow Farm with fall foliage in Pomfret, VT.

Sleepy Hollow Farm in Pomfret, Vermont during the fall season.

If you’re planning to travel to Vermont in the fall, you’ve most likely seen photos of Sleepy Hollow Farm. In fact, it’s likely one of the most photographed properties in the state! Sleepy Hollow is located a short eight-minute from Woodstock Village, down Cloudland Road in Pomfret. In recent years, this farm has absolutely exploded on Instagram, making it one of the best places to visit in Woodstock for photos.

Due to its popularity, you’ll often encounter lines of cars parked along the side of the road leading up to the property. Therefore, we suggest visiting early in the morning for the best lighting with the least crowds (especially if you’re in town on a weekend). As you may have guessed, the most popular time for visitors to photograph Sleepy Hollow is at sunset.

If you choose to visit, please remember that this location is private property. There are security gates and cameras set up for a reason; so, please do NOT trespass while taking your pictures.

Stroll the forest canopy walk at VINS Nature Center.

The Vermont Institute of Natural Science, based in Quechee, Vermont, seeks to serve the community through educating others, researching, and providing avian wildlife rehabilitation. On your visit, you can explore outdoor exhibits, featuring raptor enclosures, a songbird aviary, adventure playscape, and nature trails. Additionally, VINS recently opened the new Forest Canopy Walk! This boardwalk experience allows visitors to view the forest and the Ottauquechee River from above without actually having to make a climb. Therefore, it’s an ideal activity for the whole family, including grandparents and kids.

As you continue your way through the Center, you’ll notice two indoor exhibits: Birds Are Dinosaurs and the Forest Exhibit. Moreover, if you’re visiting with kids, you won’t want to miss the daily live bird programs, including Predators of the Sky and Raptors Up Close. For a complete list of daily events, click here. Keep in mind that the VINS Nature Center is open every day from 10 a.m. to 5 p.m. Regarding admission, tickets are $17.50 for adults, $15 for children between 4-17, and free for children 3 and under.

Go antiquing at the Vermont Antique Mall in Quechee.

The Vermont Antique Mall in Quechee, VT.

The Vermont Antique Mall in Quechee, VT.

If you’re wondering what to do in Woodstock on a rainy day, we suggest stopping by the Vermont Antique Mall! This shopping center, situated in a 17,000 sq foot barn in Quechee Gorge Village, is open daily from 10 a.m. to 5 p.m. The mall itself is actually a collection of different stores, including a souvenir shop, a Cabot cheese store, a toy museum, and antique shops. As you peruse the antique section, you’ll come across a variety of collectibles and items for the home, including books, furniture, cast iron skillets, pots, and other knick-knacks.

Where to eat in Woodstock, VT

The Prince & The Pauper Restaurant in Woodstock Village, Vermont.

The Prince & The Pauper Restaurant in Woodstock Village.

Woodstock, Vermont, has a diverse array of places to eat and experience local food. If you’re having trouble deciding where to dine, here are some of our favorite establishments in town and nearby:

  • Mon Vert Cafe is an organic cafe serving breakfast and lunch fare, artisanal coffee, and pastries. Many Woodstock visitors consider this spot to have the best breakfast in town. Quick note: Mon Vert Cafe does not take reservations and is very laid-back, so I wouldn’t try to stop by if you’re in a rush!
  • Cloudland Farm, located in Pomfret, is home to a restaurant where you can experience authentic farm-to-table dining. This locale currently offers indoor dining on Thursdays, Fridays, and Saturdays and requires reservations. As you can imagine, we suggest securing a reservation in advance if you’d like to visit on a particular day.
  • The Prince and the Pauper Restaurant offers an elegant dining experience in the center of Woodstock Village. It’s open for dinner from 5-8 p.m. on Tuesdays through Saturdays, and reservations are required for both table and bar seating. Regarding the menu, this restaurant serves a three-course Prix Fixe spread, which includes an appetizer, salad, and entrée.
  • Mountain Creamery serves the best dessert in Woodstock: homemade ice cream. If you want to try a unique flavor, order the Vermont Maple Walnut, which includes real Vermont maple syrup! Additionally, make sure to try the creamery’s seasonal flavor–it’s pumpkin ice cream in the fall. You can find a current list of flavors here.
  • Abracadabra Coffee is a pop-up coffee shop in Woodstock open on Fridays, Saturdays, and Sundays. This Vermont specialty coffee roaster is well worth a visit, serving all your coffee favorites as well as seasonal signature drinks, house-made syrups, creemees, liége waffles, and canelés.

Where to stay in Woodstock, VT

The Woodstock Inn & Resort on The Green in Woodstock, VT.

The Woodstock Inn & Resort on The Green in Woodstock, VT.

In this section, we’ll break down the best places to stay in Woodstock. Remember that Woodstock is a relatively small town, so especially during high season, it’s important to book your accommodations as soon as possible. Here are four of our preferred local hotels, all in central locations:

  • Woodstock Inn & Resort is the most famous place to stay in town, located on The Green. This historic hotel has ties to the Rockefeller family, who purchased the original inn in 1967, renovated it, and reopened the property under the same name in 1970. If you can afford to splurge on accommodations in Woodstock, this is definitely the place to do it! During the winter season, you can even go skiing at Woodstock Inn’s Suicide Six ski hill.
  • 506 On The River Inn Woodstock is a family-owned luxury resort near Woodstock Village, offering 45 rooms and suites with river and garden views. Furthermore, the property has an indoor pool, sauna, gym, game rooms, and 506 Bistro & Bar.
  • The Shire Woodstock is an independent hotel located in the heart of the Village of Woodstock. Due to its location along the Ottauquechee River, many of the property’s 50 rooms feature a scenic view. There are also a limited number of rooms with fireplaces and jacuzzis! Moreover, The Shire offers the option to book a dog-friendly suite.
  • The Blue Horse Inn is a B&B in downtown Woodstock that dates back to 1831. This Federal Greek Revival house features four categories of rooms as well as common areas such as the living room, library, dining room, music room, and back porch. Additionally, your reservation includes a three-course breakfast, non-alcoholic beverages, and a complimentary snack each afternoon.

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Learn the best things to do in Woodstock, Vermont, including top activities, hiking trails near Woodstock, covered bridges, and photo spots. | what to do in Woodstock vt

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